4-tert-Butylphenyl salicylate

Base Information

• Chemical Name: 4-tert-Butylphenyl salicylate
• CAS No.: 87-18-3
• Deprecated CAS: 138464-71-8,68027-19-0,146480-26-4,68027-19-0
• Molecular Formula: C17H18 O3
• Molecular Weight: 270.328
• European Community (EC) Number: 201-728-3
• NSC Number: 33404
• UNII: V0H9R55TGV
• DSSTox Substance ID: DTXSID9037745
• Nikkaji Number: J4.274I
• Wikidata: Q27291379
• Metabolomics Workbench ID: 49318
• ChEMBL ID: CHEMBL3186746
• Mol file: 87-18-3.mol

Synonyms:4-TBPS compound;4-tert-butylphenyl salicylate

Chemical Property of 4-tert-Butylphenyl salicylate

Chemical Property:

• Melting Point: 63°C
• Refractive Index: 1.5490 (estimate)
• Boiling Point: 373.44°C (rough estimate)
• PKA: 7.93±0.30(Predicted)
• PSA: 46.53000
• Density: 1.1141 (rough estimate)
• LogP: 3.90890
• Water Solubility.: Practically insoluble in water
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 270.125594432
• Heavy Atom Count: 20
• Complexity: 324

Purity/Quality:

96% 1H NMR ^*data from raw suppliers

4-tert-Butylphenyl Salicylate >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Moderately toxic by ingestion.
• Hazard Codes: Moderately toxic by ingestion.
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1=CC=C(C=C1)OC(=O)C2=CC=CC=C2O
• Uses: Food additive.

Technology Process of 4-tert-Butylphenyl salicylate

There total 6 articles about 4-tert-Butylphenyl salicylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

2-(4-tert-Butylphenoxy)benzoesaeure (69737-65-1) → 4-tert-butylphenyl salicylate (87-18-3)

Guidance literature:

With dipotassium hydrogenphosphate; Lumogen F Orange 240; In acetonitrile; at 40 ℃; for 26h; Irradiation; Inert atmosphere;

DOI:10.1002/anie.201706597

Reference yield: 74.0%

2-(4-(tert-butyl)phenoxy)benzaldehyde (181297-82-5) → 4-tert-butylphenyl salicylate (87-18-3)

Guidance literature:

With 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; 1,4-diaza-bicyclo[2.2.2]octane; oxygen; sodium iodide; 9-(2-mesityl)-10-methylacridinium perchlorate; In dichloromethane; at 20 ℃; for 36h; Schlenk technique; Irradiation;

DOI:10.1039/c9cc09272b

Reference yield:

para-tert-butylphenol (98-54-4) → 4-tert-butylphenyl salicylate (87-18-3)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 100 °C / Inert atmosphere

2: sodium hydroxide / water; ethanol / 16 h / Reflux

3: Lumogen F Orange 240; dipotassium hydrogenphosphate / acetonitrile / 26 h / 40 °C / Irradiation; Inert atmosphere

With dipotassium hydrogenphosphate; potassium carbonate; Lumogen F Orange 240; sodium hydroxide; In ethanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/anie.201706597

upstream raw materials:

para-tert-butylphenol

salicylic acid

2-(4-tert-Butylphenoxy)benzoesaeure

2-(4-(tert-butyl)phenoxy)benzaldehyde

Downstream raw materials:

xanth-9-one

Refernces

• 1、 Wang, Shao-Feng,Cao, Xiao-Ping,Li, Yang. "Efficient Aryl Migration from an Aryl Ether to a Carboxylic Acid Group To Form an Ester by Visible-Light Photoredox Catalysis". . p. 13809 - 13813. Retrieved 2017/10/24.